Kentucky Derby

Trying to win some money on the Derby? These are the best long shots to target.

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2020 Kentucky Derby preview

The 2020 Kentucky Derby is scheduled to be run at 7:01 p.m. Eastern Time on Saturday, Sept. 5 at Churchill Downs in Louisville. The Lexington Herald-Leader and Kentucky.com have produced all the content you need to get ready for the 146th running. Click below to get started.

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Think 3-5 morning-line favorite Tiz the Law will win this year’s Kentucky Derby going away?

That’s OK. Even if it happens, there could be money to be made with some simple bets Saturday.

There were eight 50-1 shots (and four 30-1 shots) on the morning line for the 2020 Derby, and recent history says there’s a good chance at least one of them could be lighting up the Churchill Downs tote board Saturday night. (Finnick the Fierce, one of the 50-1 shots, was scratched Friday morning).

The action on those long shots should be spread around in the trifecta and superfecta wagering. If you can manage to find the right bomber to bet, it’ll be a nice payday, even if Tiz the Law finishes first (and especially if the heavy favorite doesn’t end up winning).

Last year, Country House was declared the winner of the Derby at 65-1 odds.

The year before that, 85-1 shot Instilled Regard got up for fourth. Even with Justify and two other favorites finishing ahead of him that day, the $1 superfecta paid nearly $20,000.

Three years ago, Lookin at Lee finished second at 33-1 and Battle of Midway was third at 40-1. Favorite Always Dreaming won the race, but the $1 trifecta still paid more than $8,000.

Payouts likely won’t be that high if Tiz the Law wins — more action will be on him than past Derby favorites — but there’s still a chance to make some money.

In seven of the past 10 Kentucky Derbys, at least one of the top four finishers has gone off at odds of 30-1 or longer.

Before we break down the 50-1 shots, don’t forget about those horses at 30-1 on the morning line. Relatively lightly raced Money Moves and Max Player look especially enticing for the exotic bets. It won’t be a surprise to see Enforceable passing horses in the stretch either. All three could spice up the payouts Saturday night.

Landing one of the morning-line 50-1 shots in the top three or four could make for an even bigger payday. Here they are, ranked from worst to best (with saddle cloth/betting number in parentheses):

7. Winning Impression (14): Trainer Dallas Stewart has managed this miracle act before. He finished second with 37-1 shot Commanding Curve in 2014 and did the same with 34-1 shot Golden Soul the year before. Even with race favorites California Chrome and Orb finishing first those years, the $2 exactas paid $340 and $981, respectively. Winning Impression — with a career-best Beyer Speed Figure of 82, by far the lowest in this field — has finished seventh in each of his past two races. A top-four showing Saturday would be a much bigger shocker than either of Stewart’s previous runners-up.

6. Necker Island (11): He’s had the unenviable task of running at Art Collector, who would have been the second- or third-choice in this field if not for an injury, in two of his last three races — no shame in losing there. His numbers have been consistent, especially since moving to trainer Chris Hartman three races ago, but he’d need a major jump to make a splash against this bunch. He’s finished no better than third in any of his last seven races, and those came against a much lesser volume of talent than he’ll face Saturday.

5. Mr. Big News (9): Impressively, his speed figures have improved over every single one of his seven career races. The highlight was his win at 46-1 odds in the Oaklawn Stakes in the spring. Most recently, he was sixth — beaten more than 10 lengths — by Art Collector in the Blue Grass Stakes. Another who will need a career effort, a good trip and some clear running room late to even have a shot at hitting the board.

4. Storm the Court (4): Believe it or not, Storm the Court is the reigning champion in this group, winning top 2-year-old honors following his stunning Breeders’ Cup Juvenile victory at 45-1 odds last fall. He hasn’t won in five starts since then, though — with the exception of a flop at the Arkansas Derby — he hasn’t been too far back. Storm the Court appeared to be off the Derby trail over the summer, and he ran his last race on grass, but his connections are taking a shot at another major stunner here. Churchill Downs expert Julien Leparoux rides him for the first time, looking for his first Derby victory. Maybe he can surprise again?

3. South Bend (8): This is where things get interesting. South Bend just keeps improving and ran his highest Beyer number yet (a 97) with a fourth-place finish last time out at the Travers Stakes, a race won by Tiz the Law. That start was his first for his new trainer, Bill Mott, the Hall of Famer who won the Derby for the first time last year with Country House. South Bend has two wins in three career starts over the Churchill Downs dirt and should be just fine with the Derby distance. His style is to go to the back and make a run at the end. That could put him in a nice spot Saturday.

2. Attachment Rate (13): Trained by Churchill Downs staple Dale Romans, this son of 2007 Derby runner-up Hard Spun is another that keeps improving and could very well hit the Derby board with one more step forward. He hasn’t had the best of luck in recent races, but he was sneakily impressive in his runner-up finish to Art Collector last time out. The (very) early Derby betting Friday had him among the longest shots in the field. Don’t be surprised if he’s still running in the stretch as others fade Saturday.

1. Major Fed (5): His career-best Beyer of 87 is tied for second-lowest in this field. His last start at Churchill Downs resulted in a last-place finish in a 10-horse race. He has just one win in six career starts, and that came on Jan. 1. So, what’s to like? Well, he’s been on the wrong end of some horrific luck this year, but he just keeps running. And he should like the distance. Look for him to go to the back of the pack in Saturday’s race, then try to unleash one big run at the end while others fade from contention. He’s capable of it. It’s not a strategy that is likely to get him the roses, but it’s certainly one that has put long shots on the board on Derby Day.

Ben Roberts
Lexington Herald-Leader
Ben Roberts is the University of Kentucky men’s basketball beat writer for the Lexington Herald-Leader. He has previously specialized in UK basketball recruiting coverage and created and maintained the Next Cats blog. He is a Franklin County native and first joined the Herald-Leader in 2006. Support my work with a digital subscription
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2020 Kentucky Derby preview

The 2020 Kentucky Derby is scheduled to be run at 7:01 p.m. Eastern Time on Saturday, Sept. 5 at Churchill Downs in Louisville. The Lexington Herald-Leader and Kentucky.com have produced all the content you need to get ready for the 146th running. Click below to get started.